Water → 6-(Tert-butylthio)methyl-pyridine-3-carbonitrile

HRID 1190967ノート

反応式

HRID 1190967 の反応式
Br[CH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.[CH3:11][C:12]([SH:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(Cl)Cl>[C:12]([S:15][CH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1)([CH3:14])([CH3:13])[CH3:11]

参加物

7

反応物 4

HCID 962WaterHCID 6387tert-Butyl mercaptanHCID 10796Cesium carbonateHCID 219277766-(Bromomethyl)pyridine-3-carbonitrile

生成物 1

HCID 584955036-(Tert-butylthio)methyl-pyridine-3-carbonitrile収率 76%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

Dissolve 6-bromomethyl-pyridine-3-carbonitrile (6.2 g, 31.4 mmol) in anhydrous DMF (60 mL) under nitrogen. Add tert-butylthiol (5.32 mL, 47.2 mmol) followed by cesium carbonate (15.3 g, 47.2 mmol) and stir the resulting suspension overnight. Dissolve the reaction mixture in DCM (200 mL) and add water (200 mL). Extract the aqueous phase with DCM (2×200 mL) and dry the combined organic extracts over MgSO4. Filter, add silica gel and concentrate the mixture in vacuo. Purify the residue by chromatography on silica gel (40 g) eluting with cyclohexane/EtOAc (98:2 to 65:35 gradient) to obtain the desired material as a yellow solid (4.92 g, 76%). MS (ES+) m/z: 207 (M+H)+.

後処理

  1. extractionExtract the aqueous phase with DCM (2×200 mL)
  2. dry with materialdry the combined organic extracts over MgSO4
  3. filtrationFilter
  4. additionadd silica gel
  5. concentrationconcentrate the mixture in vacuo
  6. customPurify the residue by chromatography on silica gel (40 g)
  7. washeluting with cyclohexane/EtOAc (98:2 to 65:35 gradient)

出典と根拠

ORDレコード
ord-c31941f3b78f4f8c88108a028e0da764
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

反応ノート

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